rac-2-Methyl­amino-1,2-diphenyl­ethanol

Bari, A.; Al-Obaid, A.M.; Ng, S.W.

doi:10.1107/S1600536812002012

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o492

doi:10.1107/S1600536812002012

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rac-2-Methylamino-1,2-diphenylethanol

Ahmed Bari,^a Abdulrahman M. Al-Obaid ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 January 2012; accepted 16 January 2012; online 21 January 2012)

The dihedral angle between the two phenyl rings in the title compound, C₁₅H₁₇NO, is 52.9 (1)°. In the crystal, the molecules are connected by O—H⋯N hydrogen bonds into centrosymmetric dimers. The amino H atom is not involved in hydrogen bonding.

Related literature

For the use of chiral 2-(2-methylamino)-1,2-diphenylethan-1-ol in organic synthesis, see: Gamsey et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₇NO
M_r = 227.30
Monoclinic, C 2/c
a = 27.4279 (7) Å
b = 5.69216 (11) Å
c = 17.1910 (5) Å
β = 116.223 (3)°
V = 2407.69 (10) Å³
Z = 8
Cu Kα radiation
μ = 0.61 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.838, T_max = 0.942
4176 measured reflections
2373 independent reflections
2197 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.03
2373 reflections
164 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1ⁱ	0.92 (2)	1.88 (2)	2.799 (1)	172 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002012/bt5789sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002012/bt5789Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002012/bt5789Isup3.cml

checkCIF report

Comment top

Optically active 2-(2-methylamino)-1,2-diphenylethanol is used in asymmetric synthesis, e.g., the asymmetric hydrogenation of chiral vinyloxazaboralidines (Gamsey et al., 2004). The unsubstitued homolog is used for the palladium-assisted chiral tandem alkylation and carbonylative coupling reactions. The crystal structure of the racemic 2-(metahylamino)-1,2-diphenylethanol (Scheme I) is presented here.

The aromatic rings of the ethyl chain are staggered, the twist being 52.9 (1) °. The hydroxy group is hydrogen-bond donor to the amino group of an adjacent molecule; the amino group is hydrogen-bond donor to the hydroxy group of another molecule. The hydrogen bonds generate a linear chain running along [0 1 0] (Table 1).

Related literature top

For the use of chiral 2-(2-methylamino)-1,2-diphenylethan-1-ol in organic synthesis, see: Gamsey et al. (2004).

Experimental top

The compound was obtained commercially, and crystals were grown from its solution in ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₅H₁₇NO at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

rac-2-Methylamino-1,2-diphenylethanol top

Crystal data top

C₁₅H₁₇NO	F(000) = 976
M_r = 227.30	D_x = 1.254 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 2861 reflections
a = 27.4279 (7) Å	θ = 2.9–74.3°
b = 5.69216 (11) Å	µ = 0.61 mm⁻¹
c = 17.1910 (5) Å	T = 100 K
β = 116.223 (3)°	Prism, colorless
V = 2407.69 (10) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2373 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2197 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.014
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.5°, θ_min = 3.6°
ω scan	h = −26→34
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→4
T_min = 0.838, T_max = 0.942	l = −19→21
4176 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0476P)² + 1.6566P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2373 reflections	Δρ_max = 0.29 e Å⁻³
164 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (2)

Crystal data top

C₁₅H₁₇NO	V = 2407.69 (10) Å³
M_r = 227.30	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 27.4279 (7) Å	µ = 0.61 mm⁻¹
b = 5.69216 (11) Å	T = 100 K
c = 17.1910 (5) Å	0.30 × 0.20 × 0.10 mm
β = 116.223 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2373 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2197 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.942	R_int = 0.014
4176 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.29 e Å⁻³
2373 reflections	Δρ_min = −0.22 e Å⁻³
164 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.56414 (3)	0.35675 (13)	0.57996 (5)	0.0187 (2)
N1	0.49951 (4)	0.73117 (17)	0.59666 (6)	0.0174 (2)
C1	0.57758 (4)	0.59658 (19)	0.57561 (7)	0.0159 (2)
H1	0.5564	0.6491	0.5142	0.019*
C2	0.55920 (4)	0.74825 (18)	0.63208 (7)	0.0152 (2)
H2	0.5679	0.9151	0.6250	0.018*
C3	0.63724 (4)	0.63255 (19)	0.59947 (6)	0.0157 (2)
C4	0.67644 (4)	0.46581 (19)	0.64578 (7)	0.0178 (2)
H4	0.6660	0.3244	0.6637	0.021*
C5	0.73091 (5)	0.5046 (2)	0.66609 (7)	0.0201 (3)
H5	0.7574	0.3897	0.6977	0.024*
C6	0.74656 (4)	0.7110 (2)	0.64018 (7)	0.0198 (3)
H6	0.7836	0.7365	0.6535	0.024*
C7	0.70781 (5)	0.8798 (2)	0.59482 (7)	0.0196 (3)
H7	0.7184	1.0217	0.5774	0.023*
C8	0.65356 (4)	0.84107 (19)	0.57486 (7)	0.0183 (2)
H8	0.6272	0.9575	0.5441	0.022*
C9	0.58952 (4)	0.69014 (19)	0.72835 (7)	0.0156 (2)
C10	0.57931 (5)	0.4847 (2)	0.76303 (7)	0.0203 (3)
H10	0.5521	0.3788	0.7263	0.024*
C11	0.60851 (5)	0.4332 (2)	0.85085 (7)	0.0220 (3)
H11	0.6011	0.2927	0.8735	0.026*
C12	0.64843 (5)	0.5860 (2)	0.90549 (7)	0.0215 (3)
H12	0.6685	0.5504	0.9654	0.026*
C13	0.65873 (4)	0.7908 (2)	0.87190 (7)	0.0217 (3)
H13	0.6859	0.8965	0.9089	0.026*
C14	0.62935 (4)	0.8422 (2)	0.78388 (7)	0.0184 (2)
H14	0.6367	0.9834	0.7615	0.022*
C15	0.47651 (5)	0.9274 (2)	0.62451 (7)	0.0219 (3)
H15A	0.4381	0.8962	0.6083	0.033*
H15B	0.4798	1.0722	0.5963	0.033*
H15C	0.4963	0.9453	0.6876	0.033*
H1O	0.5420 (7)	0.316 (3)	0.5233 (12)	0.047 (5)*
H1N	0.4909 (6)	0.597 (3)	0.6155 (9)	0.027 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0215 (4)	0.0148 (4)	0.0180 (4)	−0.0025 (3)	0.0070 (3)	−0.0017 (3)
N1	0.0150 (4)	0.0174 (5)	0.0190 (5)	−0.0005 (3)	0.0067 (4)	0.0003 (4)
C1	0.0181 (5)	0.0147 (5)	0.0137 (5)	−0.0001 (4)	0.0059 (4)	0.0001 (4)
C2	0.0149 (5)	0.0147 (5)	0.0153 (5)	−0.0006 (4)	0.0060 (4)	−0.0001 (4)
C3	0.0189 (5)	0.0170 (5)	0.0118 (5)	0.0000 (4)	0.0073 (4)	−0.0027 (4)
C4	0.0211 (5)	0.0176 (5)	0.0160 (5)	0.0003 (4)	0.0094 (4)	−0.0001 (4)
C5	0.0199 (5)	0.0219 (6)	0.0183 (5)	0.0044 (4)	0.0084 (4)	0.0010 (4)
C6	0.0185 (5)	0.0239 (6)	0.0184 (5)	−0.0002 (4)	0.0094 (4)	−0.0029 (4)
C7	0.0229 (6)	0.0186 (5)	0.0193 (5)	−0.0027 (4)	0.0112 (5)	−0.0013 (4)
C8	0.0207 (5)	0.0178 (5)	0.0161 (5)	0.0018 (4)	0.0077 (4)	0.0006 (4)
C9	0.0161 (5)	0.0168 (5)	0.0153 (5)	0.0020 (4)	0.0082 (4)	−0.0008 (4)
C10	0.0233 (6)	0.0179 (6)	0.0188 (5)	−0.0033 (4)	0.0085 (5)	−0.0019 (4)
C11	0.0283 (6)	0.0191 (6)	0.0210 (6)	0.0010 (5)	0.0131 (5)	0.0032 (4)
C12	0.0219 (5)	0.0283 (6)	0.0151 (5)	0.0034 (5)	0.0088 (4)	0.0025 (4)
C13	0.0192 (5)	0.0290 (6)	0.0164 (5)	−0.0050 (5)	0.0075 (5)	−0.0029 (5)
C14	0.0195 (5)	0.0193 (5)	0.0182 (5)	−0.0025 (4)	0.0098 (4)	−0.0004 (4)
C15	0.0203 (5)	0.0264 (6)	0.0196 (6)	0.0037 (4)	0.0093 (5)	−0.0008 (4)

Geometric parameters (Å, º) top

O1—C1	1.4246 (13)	C7—C8	1.3888 (15)
O1—H1o	0.922 (18)	C7—H7	0.9500
N1—C15	1.4636 (14)	C8—H8	0.9500
N1—C2	1.4764 (13)	C9—C14	1.3900 (15)
N1—H1n	0.899 (15)	C9—C10	1.3961 (15)
C1—C3	1.5147 (14)	C10—C11	1.3922 (16)
C1—C2	1.5409 (14)	C10—H10	0.9500
C1—H1	1.0000	C11—C12	1.3889 (17)
C2—C9	1.5242 (14)	C11—H11	0.9500
C2—H2	1.0000	C12—C13	1.3842 (16)
C3—C4	1.3907 (15)	C12—H12	0.9500
C3—C8	1.3985 (15)	C13—C14	1.3953 (15)
C4—C5	1.3934 (15)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.3900 (16)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.3887 (16)	C15—H15C	0.9800
C6—H6	0.9500

C1—O1—H1O	104.6 (11)	C6—C7—H7	120.0
C15—N1—C2	111.99 (9)	C8—C7—H7	120.0
C15—N1—H1N	107.9 (9)	C7—C8—C3	120.75 (10)
C2—N1—H1N	109.2 (9)	C7—C8—H8	119.6
O1—C1—C3	112.89 (8)	C3—C8—H8	119.6
O1—C1—C2	109.85 (8)	C14—C9—C10	118.25 (10)
C3—C1—C2	111.63 (8)	C14—C9—C2	119.79 (9)
O1—C1—H1	107.4	C10—C9—C2	121.95 (10)
C3—C1—H1	107.4	C11—C10—C9	120.78 (10)
C2—C1—H1	107.4	C11—C10—H10	119.6
N1—C2—C9	114.03 (8)	C9—C10—H10	119.6
N1—C2—C1	108.37 (8)	C12—C11—C10	120.36 (11)
C9—C2—C1	112.89 (8)	C12—C11—H11	119.8
N1—C2—H2	107.1	C10—C11—H11	119.8
C9—C2—H2	107.1	C13—C12—C11	119.37 (10)
C1—C2—H2	107.1	C13—C12—H12	120.3
C4—C3—C8	118.85 (10)	C11—C12—H12	120.3
C4—C3—C1	122.15 (10)	C12—C13—C14	120.16 (11)
C8—C3—C1	119.00 (9)	C12—C13—H13	119.9
C3—C4—C5	120.48 (10)	C14—C13—H13	119.9
C3—C4—H4	119.8	C13—C14—C9	121.09 (10)
C5—C4—H4	119.8	C13—C14—H14	119.5
C6—C5—C4	120.17 (10)	C9—C14—H14	119.5
C6—C5—H5	119.9	N1—C15—H15A	109.5
C4—C5—H5	119.9	N1—C15—H15B	109.5
C7—C6—C5	119.77 (10)	H15A—C15—H15B	109.5
C7—C6—H6	120.1	N1—C15—H15C	109.5
C5—C6—H6	120.1	H15A—C15—H15C	109.5
C6—C7—C8	119.97 (10)	H15B—C15—H15C	109.5

C15—N1—C2—C9	73.91 (11)	C6—C7—C8—C3	−0.40 (16)
C15—N1—C2—C1	−159.45 (9)	C4—C3—C8—C7	1.16 (15)
O1—C1—C2—N1	−62.37 (10)	C1—C3—C8—C7	−179.41 (9)
C3—C1—C2—N1	171.61 (8)	N1—C2—C9—C14	−130.40 (10)
O1—C1—C2—C9	64.92 (11)	C1—C2—C9—C14	105.35 (11)
C3—C1—C2—C9	−61.09 (11)	N1—C2—C9—C10	50.82 (13)
O1—C1—C3—C4	−18.78 (14)	C1—C2—C9—C10	−73.43 (12)
C2—C1—C3—C4	105.54 (11)	C14—C9—C10—C11	−0.34 (16)
O1—C1—C3—C8	161.81 (9)	C2—C9—C10—C11	178.45 (10)
C2—C1—C3—C8	−73.87 (12)	C9—C10—C11—C12	−0.04 (17)
C8—C3—C4—C5	−0.97 (15)	C10—C11—C12—C13	0.32 (17)
C1—C3—C4—C5	179.62 (10)	C11—C12—C13—C14	−0.23 (17)
C3—C4—C5—C6	0.04 (16)	C12—C13—C14—C9	−0.16 (17)
C4—C5—C6—C7	0.74 (16)	C10—C9—C14—C13	0.44 (16)
C5—C6—C7—C8	−0.55 (16)	C2—C9—C14—C13	−178.38 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1ⁱ	0.92 (2)	1.88 (2)	2.799 (1)	172 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO
M_r	227.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	27.4279 (7), 5.69216 (11), 17.1910 (5)
β (°)	116.223 (3)
V (Å³)	2407.69 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.838, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	4176, 2373, 2197
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.03
No. of reflections	2373
No. of parameters	164
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1ⁱ	0.92 (2)	1.88 (2)	2.799 (1)	172 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the Research Center of Pharmacy, King Saud University, and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

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